I worry that I can lose money even if my bet is correct, if the volatility goes down and thus the premiums also go down.
Looking right now some of the options a few months out have implied volitility of 1000%+, your best bet might be selling them off on big crashes instead of waiting it out? Some of the puts I looked at went up 500%+ after this dip
Yeah, that occurred to me. At least sell off enough that I don't mind letting the rest ride.